KR20140142807A - Novel composition, electrode and solar cell comprising the same - Google Patents
Novel composition, electrode and solar cell comprising the same Download PDFInfo
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
Description
The present invention relates to a novel compound, an electrode including the same, and a solar cell including the same.
Recently, various researches have been carried out to replace existing fossil fuels in order to solve the energy problems faced. In particular, extensive research has been conducted to utilize natural energy such as wind, nuclear, or solar power to replace petroleum resources that will be depleted within decades. Among them, solar cells using solar energy are unlimited in resources and environment friendly unlike other energy sources. Since the development of Se solar cells in 1983, silicon solar cells have become popular in recent years. However, since such a silicon solar cell is very expensive to manufacture, it is difficult to put it into practical use, and it is difficult to improve the cell efficiency. In order to overcome these problems, development of a dye-sensitized solar cell having a remarkably low production cost has been actively studied.
Unlike silicon solar cells, dye-sensitized solar cells are mainly composed of photosensitive dye molecules capable of absorbing visible light to generate electron-hole pairs, and transition metal oxides transferring generated electrons as main constituent materials Photovoltaic solar cells. A representative example of dye-sensitized solar cells known so far is known from Gratzel et al., 1991, Switzerland. This battery has attracted attention because it has lower cost per electric power than conventional silicon solar cells, and thus has a function to replace conventional solar cells.
Generally, dye-sensitized solar cells use photosensitive dyes that absorb solar energy in the visible light region to produce electron-hole air. The photosensitive dye is used in a form adsorbed on a metal oxide semiconductor layer such as titanium oxide (TiO 2 ). When sunlight is absorbed in the photosensitive dye, the molecule of the photosensitive dye transitions from the ground state to the excited state, The electrons in the excited state are injected into the conduction band of the semiconductor layer, then moved to the optical electrode, which is the adjacent electrode, and then moved to the counter electrode corresponding to the anode through the external circuit. The dye molecules oxidized as a result of the electron transfer are reduced in the electrolyte, and the electrolyte ions oxidized by the dye molecule reduction reaction are reduced by reacting with electrons reaching the counter electrode. The basic principle of the dye-sensitized solar cell is to induce the generation, migration and reduction of electrons by the absorption of solar light by the photosensitive dye to perform the performance as a battery.
In order to improve the efficiency of the dye-sensitized solar cell, the larger the amount of electrons generated, the better the semiconductor layer is made thicker and the amount of the photosensitive dye adsorbed thereon is increased. However, if the thickness of the semiconductor layer is increased, the efficiency of the cell may be deteriorated because the movement distance of the electrons to be moved to the photoelectrode is increased as described above.
Therefore, there is a need for research for solving such problems and for developing a high efficiency solar cell.
TECHNICAL FIELD The present invention relates to a novel compound, an electrode including the same, and a solar cell including the same, and more particularly, to a compound for a dye-sensitized solar cell.
The present invention can provide novel compounds. As an example,
A compound having a structure represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 represents -COOR 5 or -C = C- (R 6 ) (R 7 )
Wherein R 5 represents hydrogen or an alkyl group having 1 to 4 carbon atoms, R 6 represents hydrogen or a cyano group, R 7 represents a carboxyl group,
R 2 represents -OR 8 ,
Wherein R 8 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
Ar 1 and Ar 2 each independently represent an arylene group having 6 to 12 carbon atoms or a heteroarylene group having 5 to 12 carbon atoms,
R 3 and R 4 each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
In addition, the present invention can provide an electrode comprising a compound according to the present invention.
In addition, the present invention can provide a solar cell comprising the compound according to the present invention.
A solar cell including the compound according to the present invention as an electrode can realize a high photoelectric conversion efficiency, and the lifetime can be increased through high durability.
1 is a schematic diagram of a solar cell according to the present invention, in one embodiment.
2 is a schematic view of a cathode system electrode according to an embodiment of the present invention.
3 is a schematic view of a negative electrode according to an embodiment of the present invention.
The present invention relates to a novel compound and a solar cell comprising the same, and as one example of the novel compound,
A compound having a structure represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
R 1 represents -COOR 5 or -C = C- (R 6 ) (R 7 )
Here, R 5 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
R 6 represents hydrogen or a cyano group, R 7 represents a carboxyl group,
R 2 represents -OR 8 ,
Wherein R 8 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
Ar 1 and Ar 2 each independently represent an arylene group having 6 to 12 carbon atoms or a heteroarylene group having 5 to 12 carbon atoms,
R 3 and R 4 each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms.
In the present invention, the "aryl group" includes, for example, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a naphthacenyl group, A pyrenyl group, a tolyl group, a biphenylyl group, a terphenylyl group, a chrycenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perfluorenyl group, a fluorenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, Or a phenanthrenyl group.
In addition, "alkyl group" is defined as a functional group having 1 to 4 carbon atoms derived from a linear or branched saturated hydrocarbon. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, , 2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, 2-ethylpropyl group, n-hexyl group, Methylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2- Dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2-methylpentyl group or 3-methylpentyl group.
"Heteroaryl group" refers to an "aromatic heterocycle" or "heterocyclic" derived from a monocyclic or fused ring. The heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom. Specific examples of the heteroaryl group include pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazolyl, tetrazolyl, benzotriazolyl, pyrazolyl, imidazolyl, An imidazolyl group, an isoindolyl group, an indolizinyl group, a pyridyl group, an indazolyl group, a quinolyl group, an isoquinolinyl group, a quinolizinyl group, a phthalazinyl group, a naphthyridinyl group, A carbazolyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, an imidazolyl group, A nitrogen-containing heteroaryl group including a phenanthryl group, a phenanthrolinyl group, a phenacyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, a pyrazolopyridinyl group and the like; A sulfur-containing heteroaryl group including a thienyl group, a benzothienyl group, a dibenzothienyl group and the like; An oxygen-containing heteroaryl group including a furyl group, a pyranyl group, a cyclopentapyranyl group, a benzofuranyl group, an isobenzofuranyl group, and a dibenzofuranyl group. Specific examples of the heteroaryl group include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, a phenothiazinyl group, an isoxazolyl group, a furazanyl group, a phenoxazinyl group, Compounds containing at least two heteroatoms among a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, a nitrogen atom, .
The "arylene group" may mean a divalent substituent derived from the above-described aryl group.
Further, the "heteroarylene group" may mean a divalent substituent derived from the above-mentioned heteroaryl group.
For example, in Formula 1,
R 1 represents -COOR 5 or -C = C- (R 6 ) (R 7 )
Wherein R 5 represents hydrogen, a methyl group or an ethyl group,
R 6 represents a cyano group, R 7 represents a carboxyl group,
R 2 represents -OR 8 ,
Wherein R 8 represents hydrogen, a methyl group or an ethyl group,
Ar 1 and Ar 2 each independently represent phenylene, naphthylene or furanylene,
R 3 and R 4 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.
Specifically, in Formula 1,
R 1 is -COOH, -COOCH 3 , or
R 2 represents a hydroxy or methoxy group,
Ar 1 and Ar 2 each independently represent phenylene, naphthylene or furanylene,
R 3 and R 4 may represent a phenyl group, a furanyl or a naphthyl group.
The compound represented by Formula 1 may include a structure represented by Formula 2 below.
(2)
In Formula 2,
R 9 represents -COOR 11 ,
R 10 represents -OR 12 ,
R 11 And R < 12 > may each independently represent hydrogen or a methyl group.
Specific examples of the compound represented by the formula (1) may include at least one compound selected from the group consisting of formulas (3) to (10).
[Chemical Formula 3]
[Chemical Formula 5]
[Chemical Formula 7]
[Chemical Formula 10]
The present invention can provide an electrode comprising a compound according to the present invention. For example, the electrode comprises a substrate and a metal oxide layer, and the compound can be adsorbed to the metal oxide layer. By applying an electrode containing the compound according to the present invention to an electronic device, high photoelectric conversion efficiency can be realized.
The present invention can provide a solar cell comprising the compound according to the present invention. The solar cell may be a dye-sensitized solar cell. As an example, the solar cell may have a structure in which the
For example, the
Also, the
Further, the negative electrode includes a substrate and a metal oxide layer, and the compound according to the present invention may be adsorbed on the metal oxide layer. For example, the metal oxide layer comprises a nano-sized metal oxide, and the compound according to the present invention can be adsorbed to the nano-sized metal oxide. 3, the
The stacked negative electrode is supported on a ligand solution containing the compound according to the present invention and then dried, thereby adsorbing the compound according to the present invention on the surface of the metal oxide.
Specifically, the solar cell can be manufactured by disposing the metal oxide layer of the produced anode-based electrode and the platinum layer of the anode-based electrode facing each other, and then forming a heat-resistant polymer layer and attaching and sealing the two electrodes . In addition, a fine hole passing through both the electrodes may be formed to inject the electrolyte into the space between the two electrodes.
The photoelectric conversion efficiency of the solar cell according to the present invention may be 2.0% or more. For example, the photoelectric conversion efficiency may be 2.0 to 4.5%, 2.2 to 4.0%, or 2.2 to 3.5%.
Hereinafter, the present invention will be described in more detail by way of examples and the like. The embodiments of the present invention are intended to be illustrative of the invention and are not intended to limit the scope of the invention.
Example One
Precursor manufacture
, 5 g (30.45 mmol) of 4-vinyl salicylic acid, 33.85 g (243.7 mmol) of potassium carbonate, 11.45 mL (182.25 mmol) of iodomethane and 100 mL of acetone were mixed And reacted for 80 hours. After the reaction, the insoluble solid compound was removed by filtration, and the solvent was evaporated. Then, the solid mixture was stirred for 5 minutes using 50 mL of distilled water and 50 mL of dichloromethane, and then the dichloromethane layer and the aqueous solution layer were separated. The dichloromethane solution was then dried over anhydrous MgSO 4 , filtered and the solvent was evaporated. As a result, the product was separated and purified using column chromatography to obtain a colorless oil product (2-methoxy-4-vinylbenzoate, 5.55 g, 94.8%). 1 H NMR and < 13 > C NMR data of the prepared precursor were shown below.
1 H NMR (300MHz, CDCl3) : δ 7.80 (d, J = 8.1Hz, 1H), 7.06 (d, J = 1.2Hz, 1H), 7.03 (d, J = 1.2Hz, 1H), 6.77-6.67 ( (dd, J = 0.6 Hz, 1H), 5.39 (dd, J = 0.6 Hz, 1H), 3.94 (s, 3H), 3.91 (s, 3H).
13 C NMR (300 MHz, CDCl 3): δ 166.38, 159.52, 142.89, 136.11, 132.11, 118.89, 118.01, 116.52, 109.68, 55.97, 52.00.
The product of Example 1 was prepared using the prepared precursor.
A mixture of 5.55 g (28.85 mmol) of the precursor , 14.1 g (43.3 mmol) of 4-bromo-1- ( N, N- diphenylamino) benzene, butylammonium (tetrabutylammonium chloride) 8.2 g (28.85mmol ), was in the Pd (OAc) 2 0.325 g ( 1.45 mmol), NaHCO 3 6.05 g (72.15 mmol) and 110 ℃ a mixture of 100 mL DMF was stirred for about 12 hours. Then, the insoluble solid compound was removed by filtration in DMF solution, and the solvent was evaporated. As a result, the product was purified by column chromatography (dichloromethane: methanol = 9: 1) is isolated and purified by 2-methoxy -4- [p 'product (methyl (E) of a pure yellow using a - (N, N 2-methoxy-4- [p '- ( N, N- diphenylamino) styryl] benzoate, 10.15 g, 80.8%). Melting point (mp), 1 H NMR and 13 C NMR measurement data of the compound prepared in Example 1 are shown below.
m.p: 176.1 [deg.] C
1 H NMR (300MHz, CDCl3) : δ 7.84 (d, J = 8.1Hz, 1H), 7.42 (d, J = 8.7Hz, 2H), 7.32-7.27 (m, 4H), 7.18-7.05 (m, 11H ), 6.99 (d, J = 16.2 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H).
13 C NMR (300 MHz, CDCl 3): δ 166.36, 159.73, 147.99, 147.36, 143.22, 132.31, 130.75, 130.47, 129.36, 127.69, 125.73, 124.75, 123.32, 118.06, 118.00, 109.63, 56.03, 51.97.
Example 2
10.15 g (23.3 mmol) of the product prepared in Example 1, 200 mL of dichloromethane and 30.5 mL (30.5 mmol) of boron trichloride were mixed and stirred at -78 ° C for 10 minutes And then stirred at room temperature for 10 minutes. Then, 200 mL of distilled water was added and stirred for 30 minutes, and then the dichloromethane layer and the aqueous solution layer were separated. The dichloromethane solution was then dried over anhydrous MgSO 4 , filtered and the solvent was evaporated. As a result, the product was purified by column chromatography (dichloromethane: methanol = 9: 1) is isolated and purified by 2-hydroxy -4- [p 'product (methyl (E) of a pure yellow using a - (N, N ( N, N -diphenylamino) styryl] benzoate (7.7 g, 78.1%) as a colorless oil.
Melting point (mp), 1 H NMR and 13 C NMR measurement data of the compound prepared in Example 2 are shown below.
m.p: 80 DEG C
1 H NMR (300MHz, CDCl3) : δ 10.79 (s, 1H), 7.81 (d, J = 8.4Hz, 1H), 7.41 (d, J = 8.7Hz, 2H), 7.32-7.27 (m, 6H), 7.20-7.02 (m, 10H), 6.93 (d, J = 16.2 Hz, 1H), 3.97 (s, 3H).
13 C NMR (300 MHz, CDCl 3): δ 170.38, 161.80, 148.09, 147.34, 145.12, 131.54, 130.37, 130.10, 129.35, 127.81, 125.44, 124.76, 123.33, 123.04, 117.28, 114.59. 110.86, 52.22.
Example 3
10.15 g (23.3 mmol) of the product prepared in Example 1, 116 mL (116.5 mmol) of sodium hydroxide and 250 mL of dioxane were mixed and stirred at 65 ° C for 12 hours. Then, the solvent was evaporated, and 3.6 mL of HCl (36.5%) and 500 mL of distilled water were added. The mixture was stirred for 30 minutes, and dichloromethane was added thereto, followed by further stirring for 30 minutes to obtain a dichloromethane layer and an aqueous solution layer . The dichloromethane solution was then dried over anhydrous MgSO 4 , filtered and the solvent was evaporated. As a result, the product was purified by column chromatography (dichloromethane: methanol = 9: 1) The product ((E) of the isolated and purified by using a pure yellow 2-methoxy -4- [p '- (N, N - (E) -2-methoxy-4- [p '- ( N, N- diphenylamino) styryl] benzoate, 6.98 g, 68.8%).
The melting point (mp), 1 H NMR, 13 C NMR and mass data of the compound prepared in Example 3 were measured and shown below.
m.p: 184.3 [deg.] C
1 H NMR (300MHz, CDCl3) : δ 10.74 (s, 1H), 8.16 (d, J = 8.4Hz, 1H), 7.42 (d, J = 8.7Hz, 2H), 7.33-7.23 (m, 6H), 7.16-7.06 (m, 10H), 6.99 (d, J = 16.5 Hz, 1H), 4.15 (s, 3H).
13 C NMR (300 MHz, CDCl 3): δ 165.25, 158.32, 148.36, 147.25, 144.83, 134.10, 132.01, 129.89, 129.40, 127.86, 124.83, 123.50, 123.38, 122.82, 119.87, 115.69, 109.00, 56.66
mass data: m / z (EI , CHCl 3): 421 (M +, 100%), 377 (40%).
Example 4
7.7 g (18.2 mmol) of the product prepared in Example 2, 40 mL (80.0 mmol) of 2M NaOH and 175 mL of dioxane were mixed and refluxed for 2 hours and then the solvent was evaporated. Then, 2.5 mL of HCl (36.5%), 400 mL of distilled water and 400 mL of dichloromethane were added, and the mixture was stirred for 30 minutes to separate the dichloromethane layer and the aqueous solution layer. The dichloromethane solution was then dried over anhydrous MgSO 4 , filtered and the solvent was evaporated. As a result, the product was isolated and purified by column chromatography (dichloromethane: methanol = 9: 1) to obtain a pure yellow product ((E) -4- [p '- ( N, N -diphenylamino) ( N, N- diphenylamino) styryl] salicylicacid (6.45 g, 87.2%) was obtained. The melting point (mp), 1 H NMR, 13 C NMR and mass data of the compound prepared in Example 4 were measured and shown below.
m.p: 214-215 ° C
1 H NMR (300MHz, CDCl3) : δ 10.45 (s, 1H), 7.90 (d, J = 8.7Hz, 1H), 7.41 (d, J = 8.7Hz, 2H), 7.33-7.23 (m, 6H), 7.17-7.06 (m, 10H), 6.94 (d, J = 16.2 Hz, 1H).
13 C NMR (300 MHz, CDCl 3): δ 174.61, 162.45, 148.27, 147.30, 146.47, 132.24, 131.15, 130.13, 129.38, 127.94, 125.15, 124.85, 123.42, 122.90, 117.65, 114.76, 109.64.
Mass data: m / z (EI, CHCl 3): 407 (M +, 100%), 363 (70%).
Comparative Example One
A compound according to Comparative Example 1 was prepared through the following (1) to (4).
(1) Synthesis of 1-bromo-4-iodobenzene
17.2 g of 1-bromo-4-aminobenzene and 21 mL of a hydrochloric acid aqueous solution (12 M) were mixed in a 250 mL three-neck round bottom flask. The mixed solution was put in a brine and ice-containing beaker, and the temperature was lowered to -5 ° C, and 7 g of sodium nitride aqueous solution (2.5 M) was added thereto while stirring. After 2 hours, 16 g of potassium iodide aqueous solution (2 M) was further added thereto, followed by reaction for 3 hours. The product was filtered, washed with distilled water, and then petroleum ether was eluted The 1-bromo-4-iodobenzene was isolated using silica gel column chromatography.
(2) Synthesis of N, N -diphenyl-4-bromoaniline ( N, N- diphenyl-4-bromoaniline)
A reflux condenser of 250 mL three-neck round bottom flask was installed and nitrogen gas was injected and 100 mL of a 1: 1 mixture of toluene and o-xylene , And then 11.3 g of 1-bromo-4-iodobenzene and 6.76 g of diphenylamine, 6.8 g of potassium hydroxide, 2.01 g of CuCl and 0.7 g of phenanthroline. After that, the solution was heated and refluxed at about 120 캜 for 48 hours, and after cooling, the formed product was filtered and the residual solvent was evaporated by decompression. Was separated diphenyl-4-bromoaniline (N, N -diphenyl-4- bromoaniline) - Then, petroleum ether (petroleum ether) using a silica gel column chromatography with elution agent N, N.
(3) Synthesis of 4- (diphenylamino) benzene boronic acid (4- (diphenylamino) benzene boronic acid)
After adding 80 mL of anhydrous tetrahydrofuran to a 250 mL three-neck round bottom flask and introducing nitrogen gas, 9.7 g of N, N -diphenyl-4-bromoaniline ( N, -4-bromoaniline) and 10 mL of trimethyl borate. N-butyl lithium (2.86 M in hexanes, 13.45 mL, 0.039 mol) was injected into the syringe pump at a temperature of -78 ° C by introducing the solution into a bath containing dry ice and ethanol, For one hour. It was then maintained at -78 < 0 > C for about 2 hours. Then, the mixture of dry ice and ethanol was removed, and the mixture was cooled to -10 ° C. 110 mL of 2N HCl solution was added thereto, followed by stirring at room temperature for 8 hours. The solution was then extracted three times with ether, once more with saturated NaCl solution, and then the organic layer formed was evaporated to give a solid product. The obtained product was washed with hexane and then 4- (diphenylamino) benzene boronic acid was isolated by silica gel column chromatography using ether as an eluent.
(4) Synthesis of triphenylamine salicylic acid
A 250 mL three-neck round bottom flask equipped with a reflux condenser was charged with 125 mL of a 1: 1 mixture of ethanol and distilled water, 28.9 g of triphenylamine-4-boronic acid -4-boronic acid, 32.5 g of 5-bromo salicylic acid and 0.67 g of palladium acetate (Pd (OAc) 2 ) were added and stirred at 80 ° C for 8 hours. It was then extracted with ether and the organic material evaporated to give the desired product. Then, triphenylamine salicylic acid was separated using silica gel column chromatography using ether as an eluent.
Comparative Example 2
(E) -p- (p, - (diphenylamino) styryl) benzoic acid] was prepared according to the Journal of photochemistry and photobiology A: chemistry 2011, 222, 192-202.
Manufacturing example
Cathode system Manufacture of electrodes
A transparent glass substrate on which a fluorine-doped tin oxide transparent conductive oxide layer was formed was prepared. Then, a coating composition containing titanium dioxide was applied onto the transparent conductive oxide layer of the substrate through a doctor blade method and heat-treated at 500 ° C for 30 minutes. Then, contact and filling between the nano-sized metal oxides were made to form a first metal oxide layer having a thickness of about 8 탆. Next, a coating composition containing titanium dioxide was applied to the top of the first metal oxide layer in the same manner and heat-treated at a temperature of 500 DEG C for 30 minutes to form a second metal oxide layer having a thickness of about 15 mu m. Then, a solution of a ligand in which 0.6 mM of the compounds according to Examples 1 to 4 and Comparative Examples 1 to 2 were dissolved in ethanol was prepared. The substrate on which the metal oxide layer was formed was carried thereon for 24 hours, and then dried to adsorb the dye to the nano-sized metal oxide to produce a negative electrode.
Anode system Manufacture of electrodes
A transparent glass substrate on which a fluorine-doped tin oxide transparent conductive oxide layer was formed was prepared. A 2-propanol solution in which platinum hexachloride (H 2 PtCl 6 ) was dissolved was dropped on the transparent conductive oxide layer of the substrate, and then a heat treatment was performed at 450 ° C. for 30 minutes to form a platinum layer.
Manufacture of dye-sensitized solar cell
After the nano-oxide layer of the prepared negative electrode and the platinum layer of the positive electrode were facing each other, a thermoplastic polymer layer of about 60 탆 thick made of SURLYN (Du Pont) was formed. Then, it was placed in an oven at 130 캜 for 2 minutes to attach two electrodes and then sealed. Then, a fine hole passing through the negative electrode system and the positive electrode system was formed, and an electrolyte solution was injected into the space between the two electrodes through the hole. Then, the outside of the hole was again sealed with an adhesive.
Here, the electrolyte solution was prepared by adding 0.1 M LiI, 0.05 M I 2 , 0.5 M 4-tert-butylpyridine and an ionic liquid to a 3-methoxypropionitrile solvent, (1-ethyl-1-methylpyrrolidinium iodide) dissolved in 0.6 M of phosphoric acid was prepared by dissolving 0.6 M of 1-ethyl-1-methylpyrrolidinium iodide.
Experimental Example
In the above production examples, photovoltaic conversion efficiency experiments were conducted using solar cells prepared by differentiating the compounds included in the ligand solution with the compounds according to Examples 1 to 4 and Comparative Examples 1 and 2.
At this time, photovoltaic conversion efficiencies of the solar cells containing the materials according to Examples 3 to 4 and Comparative Examples 1 and 2 in the ligand solution were tested.
The photoelectric conversion efficiency was calculated by the following equation (1). For example, the photovoltaic characteristics are observed by measuring the photovoltage and the photocurrent, and the photovoltaic conversion efficiency (η) using the current density (I sc ), the voltage (V oc ), and the fill factor (ff) e ) were calculated.
[Equation 1]
? e = (V oc x I sc x ff) / (P ine )
In the above equation (1)
(P ine ) represents 100 mW / cm < 2 > (1 sun).
The measured values are shown in Table 1 below.
As shown in Table 1, the solar cell comprising the compound according to Example 3 and Example 4 according to the present invention was compared with the solar cell including the compound according to Comparative Example 1 and Comparative Example 2 which were conventionally used And the photoelectric conversion efficiency was improved.
100: Positive electrode
110: transparent substrate
120: transparent conductive oxide layer
130: platinum layer
200: electrolyte layer
300: negative electrode
310: transparent substrate
320: transparent conductive oxide layer
330: metal oxide layer
340: metal oxide layer
Claims (9)
[Chemical Formula 1]
In Formula 1,
R 1 represents -COOR 5 or -C = C- (R 6 ) (R 7 )
Here, R 5 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
R 6 represents hydrogen or a cyano group, R 7 represents a carboxyl group,
R 2 represents -OR 8 ,
Wherein R 8 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
Ar 1 and Ar 2 each independently represent an arylene group having 6 to 12 carbon atoms or a heteroarylene group having 5 to 12 carbon atoms,
R 3 and R 4 each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms.
R 1 represents -COOR 5 or -C = C- (R 6 ) (R 7 )
Wherein R 5 represents hydrogen, a methyl group or an ethyl group,
R 6 represents a cyano group, R 7 represents a carboxyl group,
R 2 represents -OR 8 ,
Wherein R 8 represents hydrogen, a methyl group or an ethyl group,
Ar 1 and Ar 2 each independently represent phenylene, naphthylene or furanylene,
R 3 and R 4 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.
R 1 is -COOH, -COOCH 3 , or
R 2 represents a hydroxy or methoxy group,
Ar 1 and Ar 2 each independently represent phenylene, naphthylene or furanylene,
R 3 and R 4 represent a phenyl group, a furanyl group or a naphthyl group.
The compound of formula (1) comprises a structure represented by the following formula (2):
(2)
In Formula 2,
R 9 represents -COOR 11 ,
R 10 represents -OR 12 ,
R 11 And R 12 each independently represent hydrogen or a methyl group.
Wherein said compound is at least one selected from the group consisting of the following formulas (3) to (10).
[Chemical Formula 3]
[Chemical Formula 5]
[Chemical Formula 7]
[Chemical Formula 10]
The electrode comprises a substrate and a metal oxide layer,
Wherein the compound is adsorbed on the metal oxide layer.
Wherein the negative electrode contains a compound according to any one of claims 1 to 5.
The negative electrode includes a substrate and a metal oxide layer,
Wherein the compound is adsorbed on the metal oxide layer.
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| KR1020130064251A KR20140142807A (en) | 2013-06-04 | 2013-06-04 | Novel composition, electrode and solar cell comprising the same |
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| KR20160062452A (en) * | 2014-11-25 | 2016-06-02 | 삼성전자주식회사 | Method for providing graphical user interface and electronic device for supporting the same |
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| KR20160062452A (en) * | 2014-11-25 | 2016-06-02 | 삼성전자주식회사 | Method for providing graphical user interface and electronic device for supporting the same |
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